


and thank you

by bunnystomped



Series: the art of letting go [4]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Butt Plugs, Diapers, M/M, Omorashi
Language: English
Status: Completed
Published: 2021-01-31
Updated: 2021-01-31
Packaged: 2021-03-18 02:48:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,736
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28985109
Author URL: https://archiveofourown.org/users/bunnystomped/pseuds/bunnystomped
Summary: Dean’s got something extra special planned for Cas. All it involves is a gallon of water, a butt plug, and a diaper.
Relationships: Castiel/Dean Winchester
Series: the art of letting go [4]
Series URL: https://archiveofourown.org/series/2107926
Comments: 8
Kudos: 60





	and thank you

**Author's Note:**

> this is definitely the filthiest thing i've ever written.

Cas had been there for Dean through every step in this weird diaper wearing process. He’s enjoyed every step of it too, that freaky little angel. Dean can’t complain though he’s enjoyed a lot of it. But Cas has had to bear the brunt of Dean’s insecurity and today Dean wants to make his thanks known.

It started by stealing Sam’s dumb gallon water bottle. Sam was always up his ass about proper hydration. Well, he would be very hydrated today.

The next part of his plan involved a lot of lube and the giant butt plug Cas liked. Cone-shaped with soft silicone and pleasant blue color. It doesn’t matter how many times Dean shoves it up his ass it’ll always look daunting. 

He takes a long gulp from the water bottle, a twinge already evident in his bladder, before taking his clothes off and getting comfy on the bed. Truthfully, he hated prepping himself. He’d much rather have Cas do it for him but he wanted this to be a surprise. He squirts some lube, sticky and thick, onto his fingers and circles his rim slowly. He teases himself allowing his index finger to just barely penetrate his hole before pulling away. He does this for awhile letting himself work up to full hardness in anticipation. 

The first finger goes in easy enough with a sharp breath inward. He moves the finger in and out slowly, circling it inside every so often. He squirts a little more lube before adding a second finger and scissoring himself open. His insides are slick with lube and nearly stretched enough for the plug. He adds a third finger curling them inside himself right near his prostate but not far enough in to actually touch it. His cock is leaking against his stomach and he wants so badly to finish himself off right there with three fingers in his hole. He pants slightly as he grips the plug with his free hand. 

Reluctantly he removes his fingers from his hole and rolls unto his stomach hoisting himself up on his knees. With the plug doused liberally with lube, he reaches behind and nudges it against his hole. It's awkward but he manages to pop the blue plug into his loosened hole. He has to squeeze his cock to stop himself from orgasming as the plug rubs against his prostate.

The final step in his plan involves him finishing off the remains of the water bottle and putting on the diaper he altered especially for tonight. It's the same thick white diaper he's grown accustomed to wearing lately but he's cut out a decent sized hole right where his asshole is. His bladder pulses needily and he gives a longing glance towards the toilet before he tapes the diaper in place. He checks in the mirror if the cutout lines up with his hole and sure enough, the outline of the blue plug is a stark contrast to the white fluff of the diaper. Goosebumps raise up on his skin and he rushes to his phone to text Cas to get his butt to their room stat. 

He gets back on the bed positing himself so he's face down with his ass up towards the door. His cock is so hard it's peaking out the band of his diaper and he has to push it back down. 

"Dean," Cas' deep voice calls into the room followed by a sharp gasp and the door being hastily shut and locked.

"Hi, baby," Dean answers shyly. 

"Look at you," Cas says in awe. He can hear the shuffle of Cas shucking his clothes off as fast as he can. His footsteps are getting closer and then his hands are on Dean's ass rubbing it through the padding. "You look beautiful, sweetheart."

"Wanted to give you a surprise," Dean grunts when Cas pushes the palm of his hand against the plug.

"Well, I am surprised. You're wearing the plug I got you, too," Cas teases as he continues adding pressure against it.

"Yea-yuh," Dean moans. All the water he drank in preparation is finally catching up with him and he has to press a hand against his crotch to remind him not to leak but the plug's pressure against his prostate is making it more difficult than it would normally be.

"Are you okay?" Cas questions noticing Dean gripping his diapered crotch. 

"Gotta pee," Dean hisses. 

Cas chuckles at him placing a hand against his bladder and rubbing in small circles. Dean nearly collapses when he groans at the touch.

"S-st-stop," He stutters. "Wanna piss when you're inside me."

"Oh, fuck," Cas curses moving his hand away quickly. "That's so hot, Dean." 

"Glad you think so," Dean laughs. "Want this to be good for you."

"Any time spent with you is good for me, Dean," Cas says earnestly.

"Shuddup sap."

Cas hums his hand back to fiddling with the plug inside Dean. "You think you can push this out for me without wetting yourself?" He asks. 

Dean nods minutely and he grips the sheets under him for dear life. His bladder hurts and he needs to piss like a fucking racehorse, but he's got this it's fine. He braces down and feels the plug slowly move inside him. It stretches his poor hole agonizingly before coming free with a loud 'pop' and a moan from Dean. Cas lets it fall to the floor gazing into Dean's gaping hole adoringly.

"You're all pink for me," Cas coos, sinking two fingers into Dean's hole to tease his prostate. 

"Cas, please," Dean cries. "Fuck me. Please!"

"You need to go, huh?" Cas asks his fingers still deep within Dean. He pistons them in and out paying no mind to Dean's shaking legs and sweaty brow.

"Yes! You asshole!" Dean yelps, his arms giving out from holding himself up on the bed. He lays flat on his chest, ass in the air and one hand holding his poor confused penis through the diaper. His dick can't decide if it should be leaking piss or pre-cum at this point. 

"Guess I'll put you out of your misery," Cas says. Dean hears the lid of the discarded lube bottle snap open and he nearly rejoices. Cas slowly edges the tip of his cock at Dean's hole circling his hips and teasing him. 

"Please, please Cas just fuck me," Dean nearly sobs. 

At Dean's pleas, the angel finally sinks in his balls meeting Dean's ass. He stutters his hips in sharp quick movements that make Dean's breath hitch with each thrust. With a hand gripped firmly in Dean's hair he leans over and growls, "Don't go until I say."

With that Dean does let out a sob. He has to go so badly his bladder is starting to feel hot and tingly. Cas' thrusts begin to pick up pace jostling Dean across the bed like he's weightless. He's clawing at the sheets near tears from the pleasure pain of it all. 

"You look so good like this," Cas moans. "Diapered and desperate to go. But you can't until I say so. Fuck." 

"Love you, love you," Dean babbles. "Please, Cas. Love you. Needa go. So bad."

"I love you too," Cas says softly. He pulls out slowly and turns Dean around to face him. Dean's face is red and tear-streaked. "You're such a good boy."

"Needa go," Dean slurs. 

Cas moves to lean against the headboard and pats his thigh, "Come ride me, sweet boy." 

Dean shuffles on his knees towards Cas and lets the angel guide him onto his cock. The extra padding at his front rubs against Cas' bare stomach when he moves. 

"You can go Dean," Cas whispers.

"Th-thank you. Hold my hand," Dean croaks. He's fully seated on Cas' cock his knees splayed at either side of Cas' thighs and his left hand secured firmly in Cas'. He lets out a sharp gasp as he finally lets his bladder go. Cas uses his free hand to rub Dean's crotch feeling the padding as it grows sodden. 

Castiel can't help the way his hips stutter upward as the hissing of Dean releasing his bladder grows audible. "You're so hot, baby," He moans.

"It's too much," Dean cries hiding his face in Cas' neck. "It's gonna leak."

"It's fine sweet boy. You're fine," Cas encourages. "Just keep going." 

The stream goes on for what feels like ages the diaper saturated and sagging between Dean's thighs. It doesn't leak but it's the wettest Dean's ever been and Cas has never felt hotter. He grabs Dean roughly and throws him down onto the bed before thrusting into him deeply.

"You're so sexy, Dean," He growls thrusting into Dean's willing hole. Dean's arms are around his neck holding on searching for connection. Cas knows how much physical reassurance Dean needs at times and leans down to kiss him on his plump pink lips. 

Now that Dean's bladder has been voided he can finally focus on the intense pleasure Cas is giving him. Each thrust is hitting his spot expertly and his dick is straining inside his diaper begging to cum. Cas begins kneading the front of his diaper the thick padding giving Dean's cock even more friction, even more pleasure.

"Gonna cum," Dean moans.

"Mm, me too, baby," Cas says between pleasured breaths. 

With one hard thrust Dean's orgasming into his diaper his lips desperately finding Cas' to kiss him as he releases. Cas kisses him back eagerly thrusting frantically into him trying to find his own release. 

"You're so perfect, Dean," Cas cries. His balls tensing up signaling his orgasm. "You feel so amazing around me. So warm and tight."

Dean's overstimulated cries is what does Cas in and he releases deep inside Dean with a shouted moan. He rolls off Dean and lets Dean snuggle in next to him, both still panting hard. 

"You liked it?" Dean questions, his cheeks pink with embarrassment. 

It will never cease to amaze Castiel just what gets Dean's cheeks to color. His boy can be so insecure at times it breaks his heart. He squeezes Dean reassuringly, "It was amazing Dean. I loved everything about it."

He palms Dean's wet diaper, Dean shuddering in pleasure, "Especially this."

Dean paws at his hand jokingly, "You freak." 

"Dean, I think we're both a little bit freaky," Cas laughs.

Dean sighs contently, "Yeah, I guess we are."

**Author's Note:**

> as always please feel free to comment any suggestions you have for later parts <3
> 
> also if you're curious the plug dean is wearing is the grip 96 by topped toys


End file.
